127041-76-3

Upstream product

• 224434-13-3 (S)-4-Benzyl-5-hydroxy-oxazolidine-3-carboxylic acid benzyl ester 
• 1730-25-2 allylmagnesium bromide 
• 55740-07-3 (4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 24850-33-7 allyltributylstanane 
• 59830-60-3 benzyl (1S)-(1-formyl-2-phenylethyl)carbamate 
• 762-72-1 allyl-trimethyl-silane 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 501-53-1 benzyl chloroformate 
• 6372-14-1 N-((benzyloxy)carbonyl)-L-phenylalaninol 
• 1059597-07-7 (S)-benzyl 3-oxo-1-phenylhex-5-en-2-ylcarbamate 

Downstream Products

• 113283-84-4 (S)-5-Allyl-4-benzyl-oxazolidin-2-one 
• 113283-87-7 (4S,5S)-4-benzyl-5-(1-propenyl)-1,3-oxazolidin-2-one 
• 337963-40-3 (2S,3S,5S)-2-Benzyl-3-hydroxy-5-((E)-non-1-enyl)-pyrrolidine-1-carboxylic acid methyl ester 
• 337963-33-4 (2S,3S,5S)-2-Benzyl-3-hydroxy-5-hydroxymethyl-pyrrolidine-1-carboxylic acid methyl ester 
• 337963-38-9 (2S,3S)-2-Benzyl-5-hydroxymethyl-pyrrolidin-3-ol 
• 131013-30-4 (2S,3S,5R)-2-(phenylmethyl)-1-carbomethoxy-5-nonyl-3-pyrrolidinol 
• 131013-27-9 (2S,3S,5S)-5-formyl-2-(phenylmethyl)-1-carbomethoxy-3-pyrrolidinol 
• 125356-66-3 (+)-preussin 
• 113283-84-4 (4S,5R)-4-benzyl-5(1-propenyl)-1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

Selective reductions of oxazolidinones: New protocol for diastereoselective synthesis of vicinal amino alcohols

Selective reductions of oxazolidinones using sodium borohydride and their application to the diastereoselective synthesis of vicinal amino alcohols are described.

Efficient stereoselective synthesis of (2s,3s,5r)-(+)-preussin

Allyltrimethylsilane reacted with N-carbobenzoxy-L-phenylalaninal to afford with high diastereoselectivity syn-adduct which was subsequently transformed into (2S, 3S, SR)-(+)-preussin.

Eine konvergente, enantioselektive Totalsynthese von Hapalosin: ein Wirkstoff zur Vermeidung resistenter Tumorzellen in Chemotherapie

Keywords: Chemotherapie; Hapalosin; Naturstoffe; Totalsynthesen

A Novel BF3*OEt2-Catalyzed Annulation of N-Cbz-α-Amino Aldehides with Allyltrimethylsilane. Highly Stereoselective Synthesis of Cis-2,3,5-Trisubstituted Pyrrolidines

In the presence of BF3*OEt2 (0.2 molar equiv), the reactions (-10 deg C, CH2Cl2) of N-Cbz-α-amino aldehydes with allyltrimethylsilane produced pyrrolidines in good yields (70-80percent), with high all-cis stereoselectivity at the C-2, C-3, and C-5 positio

Lewis acid-mediated reaction with silyl ketene acetals and allylstannane of the aluminum acetals generated by DIBALH reduction of α-amino acid esters

The intermediates generated by DIBALH reduction of α-amino acid esters undergo condensation without racemization with silyl ketene acetals and allylstannane in the presence of Lewis acid to afford the corresponding β-hydroxy esters and homoallylic alcohol

ALUMINUM-MEDIATED ONE-POT CONVERSION OF α-AMINO ACID ESTERS TO THREO 2-AMINO ALCOHOLS WITH HIGH DIASTEREOSELECTIVITY

Reduction of N-Cbz α-amino acid esters with DIBAl-H, followed by treatment with Grignard reagent in a one-pot manner gave the corresponding threo 2-amino alcohols with high diastereoselectivity without racemization. KEYWORDS 2-amino alcohol; α-amino acid ester; DIBAL-H reduction; α-amino aldehyde; chelation controll; diastereoselective synthesis; one-pot synthesis